Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 107 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2Happy Hour Sunset Sail on Maui's Luxury Catamaran
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More
Happy Hour Sunset Sail on Maui's Luxury Catamaran
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Hawaii
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Superb100 reviews4.8
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
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Hawaii
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Superb40 reviews4.9
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion
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Hawaii
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Superb137 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay
• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 • World Famous Captain Cook Monument at Kealakekua Bay • Red Hill Area lava arches — underwater volcanic terrain, weather per... More
Kona Morning Snorkel to Captain Cook Monument at Kealakekua Bay
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Hawaii
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Superb584 reviews4.9
• Kealakekua Bay Marine Life Conservation District — 60-80 ft visibility, protected since 1969 â....
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
Waikoloa Signature Catamaran Sunset Sail
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Hawaii
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Superb421 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)
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Hawaii
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Superb61 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More
Waikiki Catamaran Snorkel with Lunch: Turtles Guaranteed
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Hawaii
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Superb2,136 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Kona Morning Snorkel to Captain Cook Monument
Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along the Kona coastline toward the Captain Cook Monument, where your adventure begins. Jump ... More
Kona Morning Snorkel to Captain Cook Monument
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Hawaii
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Superb484 reviews4.9
Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leavi....
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More
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Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
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Hawaii
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Superb374 reviews4.8
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....
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Nāpali Sunset Dinner Sail
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More
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Nāpali Sunset Dinner Sail
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Hawaii
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Superb609 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
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Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More
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Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
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Hawaii
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Superb137 reviews4.9
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....
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Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
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Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
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Hawaii
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Superb220 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Free Cancellation
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Kona Manta Ray Night Snorkel — 85–95% Sighting Rate
• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mantas seen — space available • Owner Richard Kersten pioneered the large-vessel manta ray snorkel format • Named resident manta... More
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Kona Manta Ray Night Snorkel — 85–95% Sighting Rate
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Hawaii
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Superb761 reviews4.8
• 85–95% manta ray sighting rate at Manta Village, Kona • Return free within 7 days if no mant....
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Maui Premier Whale Watching Cruise - Luxury Catamaran Experience
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More
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Maui Premier Whale Watching Cruise - Luxury Catamaran Experience
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Hawaii
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Superb89 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Free Cancellation
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Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More
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Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu
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Hawaii
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Superb64 reviews4.8
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....
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Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay
Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catamaran — and sail to the World Famous Captain Cook Monument at Kealakekua Bay, a Marine Life Conservation District on the Kona Coas... More
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Kona Afternoon Snorkel to Captain Cook Monument at Kealakekua Bay
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Hawaii
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Superb741 reviews4.9
Depart Keauhou Bay at 2:00 PM aboard the Hoku Nui — Sea Paradise’s 50-foot luxury sailing catama....
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Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
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Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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Hawaii
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Superb326 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
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Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More
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Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu
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Hawaii
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Superb1,335 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
Free Cancellation
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3 Hour Luxury Private Sailing Catamaran for 7-12 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
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Private Tour
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3 Hour Luxury Private Sailing Catamaran for 7-12 People
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Hawaii
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Superb1,335 reviews4.6
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Free Cancellation
Private Tour
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Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More
Free Cancellation
Private Tour
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Maui Molokini Snorkeling Sailing Adventure with Breakfast & Lunch
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Hawaii
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Superb223 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Free Cancellation
Private Tour
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